Structure-activity relationships of benzoxazolinones with respect to auxin-induced growth and auxin-binding protein

Masako Hoshi-Sakoda, Kenji Usui, Kozo Ishizuka, Seiji Kosemura, Shosuke Yamamura, Koji Hasegawa

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The structure-activity relationships of the naturally occurring auxin-inhibiting substance, 6-methoxy-2-benzoxazolinone, isolated from maize shoots, and its artificial analogues with respect to auxin activity and membrane-bound auxin-binding protein, were studied. 6-Isobutoxy-2-benzoxazolinone strongly inhibited auxin (1-naphthylacetic acid, NAA)-induced growth of etiolated maize coleoptile segments. 6-Isopropoxy-2-benzoxazolinone, 6-ethoxy-2-benzoxazolinone and 6-methoxy-2-benzoxazolinone showed significant inhibitory activity. However, 2-benzoxazolin-one and 6-benzyloxy-2-benzoxazolinone did not inhibit auxin-induced growth. On the basis of these data, it seemed reasonable to assume that the auxin-inhibitory activity was enhanced by increasing the side chain length at position C-6 on the 2-benzoxazolinone, although the attachment of a ring at C-6 destroyed activity. Competition by benzoxazolinones with an alkoxy group at C-6 with 3H-NAA at auxin-binding protein(s) isolated from endoplasmic reticulum (ER) membrane of maize shoots showed a positive correlation with their physiological effects. However, since the inhibitory activity of the benzoxazolinones for auxin-receptor(s) binding was small compared with their physiological activity, the benzoxazolinones may contribute to inhibition of auxin-induced growth through interference with other auxin-receptors.

Original languageEnglish
Pages (from-to)297-300
Number of pages4
JournalPhytochemistry
Volume37
Issue number2
DOIs
Publication statusPublished - 1994

Fingerprint

Indoleacetic Acids
structure-activity relationships
Structure-Activity Relationship
binding proteins
auxins
Carrier Proteins
Growth
Zea mays
naphthaleneacetic acid
corn
Membranes
receptors
shoots
Cotyledon
coleoptiles
Chain length
Endoplasmic Reticulum
endoplasmic reticulum
benzoxazolone

Keywords

  • antiauxin
  • auxin-binding protein
  • benzoxazolinone
  • Gramineae
  • structure-activity relationships.
  • Zea mays

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

Structure-activity relationships of benzoxazolinones with respect to auxin-induced growth and auxin-binding protein. / Hoshi-Sakoda, Masako; Usui, Kenji; Ishizuka, Kozo; Kosemura, Seiji; Yamamura, Shosuke; Hasegawa, Koji.

In: Phytochemistry, Vol. 37, No. 2, 1994, p. 297-300.

Research output: Contribution to journalArticle

Hoshi-Sakoda, Masako ; Usui, Kenji ; Ishizuka, Kozo ; Kosemura, Seiji ; Yamamura, Shosuke ; Hasegawa, Koji. / Structure-activity relationships of benzoxazolinones with respect to auxin-induced growth and auxin-binding protein. In: Phytochemistry. 1994 ; Vol. 37, No. 2. pp. 297-300.
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